Novel aromatic compound and organic electroluminescent element containing the same

ABSTRACT

A novel aromatic compound having an anthracene skeleton structure and an asymmetric molecular structure; and an organic electroluminescence device which comprises a cathode, an anode and an organic thin film layer comprising at least one layer containing a light emitting layer and sandwiched between the cathode and the anode in which at least one layer in the organic thin film layer contains the above novel aromatic compound singly or as a component of a mixture. The organic electroluminescence device exhibits a great luminance of emitted light, a great efficiency of light emission and a high purity of color, emits bluish light, is excellent in stability at high temperatures and has a long life. The organic electroluminescence device can be provided by utilizing the novel aromatic compound.

The present application is a Continuation Application of Ser. No.10/508,602, filed Mar. 16, 2005, which was a national stage entry ofInternational Application PCT/JP03/04905, filed Apr. 17, 2003, whichclaims priority to Japanese Patent Application No. 2002-114400, filedApr. 17, 2002.

TECHNICAL FIELD

The present invention relates to a novel aromatic compound and anorganic electroluminescent (“electroluminescent” and“electro-luminescence” will be referred to as “EL”, hereinafter) devicecontaining the compound and, more particularly, to a novel aromaticcompound which can provide an organic EL device exhibiting a greatluminance of emitted light, a great efficiency of light emission and ahigh purity of color, emitting bluish light, excellent in stability athigh temperatures and having a long life and an organic EL deviceutilizing the compound.

BACKGROUND ART

An organic EL device is a spontaneous light emitting device whichutilizes the principle that a fluorescent substance emits light byenergy of recombination of holes injected from an anode and electronsinjected from a cathode when an electric field is applied. Since anorganic EL device of the laminate type driven under a low electricvoltage was reported by C. W. Tang of Eastman Kodak Company (C. W. Tangand S. A. Vanslyke, Applied Physics Letters, Volume 51, Pages 913,1987), many studies have been conducted on organic EL devices usingorganic materials as the constituting materials. Tang et al. used alaminate structure using tris(8-hydroxyquinolinol)aluminum for the lightemitting layer and a triphenyldiamine derivative for the holetransporting layer. Advantages of the laminate structure are that theefficiency of hole injection into the light emitting layer can beincreased, that the efficiency of forming excited particles which areformed by blocking and recombining electrons injected from the cathodecan be increased, and that excited particles formed within the lightemitting layer can be enclosed. As the structure of the organic ELdevice, a two-layered structure having a hole transporting (injecting)layer and an electron transporting and light emitting layer and athree-layered structure having a hole transporting (injecting) layer, alight emitting layer and an electron transporting (injecting) layer arewell known. To increase the efficiency of recombination of injectedholes and electrons in the devices of the laminate type, the structureof the device and the process for forming the device have been studied.

As the light emitting material, chelate complexes such astris(8-quinolinolato)aluminum, coumarine derivatives,tetraphenyl-butadiene derivatives, bisstyrylarylene derivatives andoxadiazole derivatives are known. It is reported that light in thevisible region ranging from blue light to red light can be obtained byusing these light emitting materials, and development of a deviceexhibiting color images is expected (For example, Japanese PatentApplication Laid-Open Nos. Heisei 8 (1996)-239655, Heisei 7(1995)-138561 and Heisei 3 (1991)-200889).

A device using a phenylanthracene derivative as the light emittingmaterial is disclosed in Japanese Patent Application Laid-Open No.Heisei 8 (1996)-012600. Although the anthracene derivative is used asthe material for emitting bluish light, a further improvement in theefficiency of light emission has been desired. On the other hand, animprovement in the stability of the thin film has been desired so thatthe life of the device is increased. However, heretofore knownanthracene derivatives form crystals in many cases to cause fracture ofthe thin film, and the improvement has been desired. For example, adinaphthylanthracene compound is disclosed in the U.S. Pat. No.0,593,571. However, since this compound has a symmetric molecularstructure in the horizontal and vertical directions, the molecules areeasily arranged to form crystals during storage at high temperatures anddriving at high temperatures. Japanese Patent Application Laid-Open No.Heisei 2000-273056 discloses an allylanthracene compound asymmetric inthe horizontal direction. However, one of the groups as substituents tothe anthracendiyl group is a simple group such as phenyl group andbiphenyl group, and the crystallization cannot be prevented.

DISCLOSURE OF THE INVENTION

The present invention has been made to overcome the above problems andhas an object of providing a novel aromatic compound which can providean organic EL device exhibiting a great luminance of emitted light, agreat efficiency of light emission and a high purity of color, emittingbluish light, excellent in stability at high temperatures and having along life and an organic EL device utilizing the compound.

As the result of intensive studies by the present inventors to overcomethe above problems, it was found that the above problems could beovercome by using a compound which has a high glass transitiontemperature and an asymmetric molecular structure as the material forthe organic thin film layer of an organic EL device. The presentinvention has been completed based on this knowledge.

The present invention provides a novel aromatic compound represented byfollowing general formula (A) or (B).

General formula (A) is:

A-Ar—B  (A)

wherein Ar represents a substituted or unsubstituted anthracendiylgroup, B represents a heterocyclic group which has 2 to 60 carbon atomsor a substituted or unsubstituted aryl group having 5 to 60 carbon atomseach of which is mono-substituted with an alkenyl group or an arylaminogroup, A represents a group which is selected from groups represented bythe following general formulae (1) to (11):

wherein Ar₁ to Ar₃ each independently represent a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, Ar₄ represents asubstituted or unsubstituted arylene group having 6 to 30 carbon atoms,Ar₅ represents a substituted or unsubstituted trivalent aromatic residuegroup having 6 to 30 carbon atoms, R₁ and R₂ each independentlyrepresent hydrogen atom, a halogen atom, hydroxyl group, a substitutedor unsubstituted amino group, nitro group, cyano group, a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted alkenyl group having 2 to 40 carbon atoms, a substitutedor unsubstituted cycloalkyl group having 5 to 40 carbon atoms, asubstituted or unsubstituted alkoxyl group having 1 to 30 carbon atoms,a substituted or unsubstituted aromatic hydrocarbon group having 5 to 40carbon atoms, a substituted or unsubstituted aromatic heterocyclic grouphaving 2 to 40 carbon atoms, a substituted or unsubstituted aralkylgroup having 7 to 40 carbon atoms, a substituted or unsubstitutedaryloxyl group having 6 to 40 carbon atoms, a substituted orunsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, asubstituted or unsubstituted silyl group having 3 to 40 carbon atoms orcarboxyl group, and groups represented by Ar₁ and Ar₂ and groupsrepresented by R₁ and R₂ each independently may be bonded to each otherand form a cyclic structure;the foregoing general formulae (1) to (11) may be substituted withsubstituted or unsubstituted alkyl groups having 1 to 30 carbon atoms orsubstituted or unsubstituted phenyl group; andA does not represent phenyl group substituted with an arylamino groupwhen the group represented by B is substituted with an arylamino group.

General formula (B) is:

A′-Ar—Ar—B  (B)

wherein Ar represents a substituted or unsubstituted anthracendiylgroup, B represents a heterocyclic group which has 2 to 60 carbon atomsor a substituted or unsubstituted aryl group having 5 to 60 carbon atomseach of which is mono-substituted with an alkenyl group or an arylaminogroup, A′ represents a group which is selected from groups representedby the following general formulae (2) to (12):

wherein Ar₁ to Ar₃ each independently represent a substituted orunsubstituted aryl group having 6 to 30 carbon atoms, Ar₄ represents asubstituted or unsubstituted arylene group having 6 to 30 carbon atoms,Ar₅ represents a substituted or unsubstituted trivalent aromatic residuegroup having 6 to 30 carbon atoms, R₁ and R₂ each independentlyrepresent hydrogen atom, a halogen atom, hydroxyl group, a substitutedor unsubstituted amino group, nitro group, cyano group, a substituted orunsubstituted alkyl group having 1 to 30 carbon atoms, a substituted orunsubstituted alkenyl group having 2 to 40 carbon atoms, a substitutedor unsubstituted cycloalkyl group having 5 to 40 carbon atoms, asubstituted or unsubstituted alkoxyl group having 1 to 30 carbon atoms,a substituted or unsubstituted aromatic hydrocarbon group having 5 to 40carbon atoms, a substituted or unsubstituted aromatic heterocyclic grouphaving 2 to 40 carbon atoms, a substituted or unsubstituted aralkylgroup having 7 to 40 carbon atoms, a substituted or unsubstitutedaryloxyl group having 6 to 40 carbon atoms, a substituted orunsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, asubstituted or unsubstituted silyl group having 3 to 40 carbon atoms orcarboxyl group, groups represented by Ar₁ and Ar₂ and groups representedby R₁ and R₂ each independently may be bonded to each other and form acyclic structure, and p in general formula (12) represents 0 or 1;the foregoing general formulae (1) to (11) may be substituted withsubstituted or unsubstituted alkyl groups having 1 to 30 carbon atoms orsubstituted or unsubstituted phenyl group; andA does not represent phenyl group substituted with an arylamino groupwhen the group represented by B is substituted with an arylamino group.

The present invention also provides an organic EL device which comprisesa cathode, an anode and an organic thin film layer comprising at leastone layer containing a light emitting layer and sandwiched between thecathode and the anode, wherein at least one layer in the organic thinfilm layer comprises a novel aromatic compound represented by generalformula (A) or (B) singly or as a component of a mixture.

THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION

The present invention provides a novel compound represented by thefollowing general formula (A) or (B):

A-Ar—B  (A)

A′-Ar—Ar—B  (B)

In the above general formulae (A) and (B), Ar represents a substitutedor unsubstituted anthracendiyl group.

In the above general formulae (A) and (B), B represents a heterocyclicgroup which has 2 to 60 carbon atoms or a substituted or unsubstitutedaryl group having 5 to 60 carbon atoms each of which is monosubstitutedwith an alkenyl group or an arylamino group. It is preferable that Brepresents a heterocyclic group which has 2 to 60 carbon atoms and ismonosubstituted with an alkenyl group or an arylamino group or an arylgroup which has 5 to 60 carbon atoms and is monosubstituted with analkenyl group or an arylamino group.

Examples of the alkenyl group as the substituent in the grouprepresented by B include vinyl group, allyl group, 1-butenyl group,2-butenyl group, 3-butenyl group, 1,3-butadienyl group, 1-methylvinylgroup, styryl group, 2,2-diphenylvinyl group, 2,2-ditolylvinyl group,1,2-ditolylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group,2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group,3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group,1-phenyl-1-butenyl group and 3-phenyl-1-butenyl group.

Examples of the arylamino group as the substituent in the grouprepresented by B include phenylamino group, diphenylamino group,biphenylamino group, naphthylamino group, anthranylamino group,ditolylamino group, dinaphthylamino group, phenylnaphthylamino group,phenylmethylamino group, pyrenylphenylamino group, biphenylamino groupand biphenylnaphthylamino group.

Examples of the substituted or unsubstituted heterocyclic group as thesubstituent in the group represented by B include 1-pyrrolyl group,2-pyrrolyl group, 3-pyrrolyl group, pyradinyl group, 2-pyridinyl group,3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indolyl group,3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group,7-indolyl group, 1 isoindolyl group, 2-isoindolyl group, 3-isoindolylgroup, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group,7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group,3-benzofuranyl group, 4-benzofuranyl group, 5-benzofuranyl group,6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group,3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranylgroup, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolylgroup, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolylgroup, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group,3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group,6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group,2-quinoxanyl group, 5-quinoxanyl group, 6-quinoxanyl group, 1-carbazolylgroup, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group,9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group,3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenanthridinylgroup, 7-phenanthridinyl group, 8-phenanthridinyl group,9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group,2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinylgroup, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group,1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group,1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group,1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group,1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group,1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group,1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group,1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group,1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group,1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group,1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group,1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group,1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group,1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group,2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group,2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group,2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group,2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group,2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group,2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group,2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group,2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group,2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group,2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group,2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group,2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group,1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group,2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group,10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group,3-phenoxazinyl group, 4-phenoxazinyl group, 10-phenoxazinyl group,2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolylgroup, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group,3-thienyl group, 2-methylpyrrol-1-yl group, 2-methylpyrrol-3-yl group,2-methylpyrrol-4-yl group, 2-methyl-pyrrol-5-yl group,3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group,3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group,2-t-butylpyrrol-4-yl group, 3-(2-phenylpropyl)pyrrol-1-yl group,2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolylgroup, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group,4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group and4-t-butyl-3-indolyl group. The above group has 2 to 60 carbon atomsincluding the above substituents.

Examples of the aryl group represented by B include phenyl group,naphthyl group, anthranyl group, phenanthryl group, pyrenyl group,coronyl group, biphenyl group, terphenyl group, pyrrolyl group, furanylgroup, thiophenyl group, benzothiophenyl group, oxadiazolyl group,diphenylanthranyl group, indolyl group, carbazolyl group, pyridyl group,benzoquinolyl group, fluoranthenyl group and acenaphthofluoranthenylgroup. The above group has 5 to 60 carbon atoms including the abovesubstituents.

In the above general formula (A), A represents a group which is selectedfrom groups represented by general formulae (1) to (11):

In general formulae (1) to (11), Ar₁ to Ar₃ each independently representa substituted or unsubstituted aryl group having 6 to 30 carbon atoms,Ar₄ represents a substituted or unsubstituted arylene group having 6 to30 carbon atoms, Ar₅ represents a substituted or unsubstituted trivalentaromatic residue group having 6 to 30 carbon atoms, and R₁ and R₂ eachindependently represent hydrogen atom, a halogen atom, hydroxyl group, asubstituted or unsubstituted amino group, nitro group, cyano group, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted alkenyl group having 2 to 40 carbon atoms,a substituted or unsubstituted cycloalkyl group having 5 to 40 carbonatoms, a substituted or unsubstituted alkoxyl group having 1 to 30carbon atoms, a substituted or unsubstituted aromatic hydrocarbon grouphaving 5 to 40 carbon atoms, a substituted or unsubstituted aromaticheterocyclic group having 2 to 40 carbon atoms, a substituted orunsubstituted aralkyl group having 7 to 40 carbon atoms, a substitutedor unsubstituted aryloxyl group having 6 to 40 carbon atoms, asubstituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbonatoms, a substituted or unsubstituted silyl group having 3 to 40 carbonatoms or carboxyl group. Groups represented by Ar₁ and Ar₂ and groupsrepresented by R₁ and R₂ each independently may be bonded to each otherand form a cyclic structure.

The foregoing general formulae (1) to (11) may be substituted withsubstituted or unsubstituted alkyl groups having 1 to 30 carbon atoms orsubstituted or unsubstituted phenyl group, and in the above generalformula (A), A does not represent phenyl group substituted with anarylamino group when the group represented by B is substituted with anarylamino group.

Examples of the substituted or unsubstituted aryl groups having 6 to 30carbon atoms which is represented by Ar₁ to Ar₃ include phenyl group,naphthyl group, anthranyl group, phenanthryl group, pyrenyl group,coronyl group, biphenyl group, terphenyl group, pyrrolyl group, furanylgroup, thiophenyl group, benzothiophenyl group, oxathiazolyl group,diphenylanthranyl group, indolyl group, carbazolyl group, pyridyl group,benzoquinolyl group, fluoranthenyl group and acenaphthofluoranthenylgroup.

Examples of the substituted or unsubstituted arylene groups having 6 to30 carbon atoms which is represented by Ar₄ include phenylene group,naphthylene group, anthranylene group, phenanthrylene group, pyrenylenegroup, coronylene group, biphenylene group, terphenylene group,pyrrolylene group, furanylene group, thiophenylene group,benzothiophenylene group, oxadiazolylene group, diphenyl-anthranylenegroup, indolylene group, carbazolylene group, pyridylene group,benzoquinolylene group, fluoranthenylene group andacenaphtho-fluoranthenylene group.

Examples of the halogen atom represented by R₁ and R₂ include fluorineatom, chlorine atom, bromine atom and iodine atom.

Examples of the substituted or unsubstituted amino groups represented byR₁ and R₂ are groups represented by —NX¹X². For example, X¹ and X² eachindependently represent hydrogen atom, methyl group, ethyl group, propylgroup, isopropyl group, n-butyl group, s-butyl group, isobutyl group,t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octylgroup, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group,2-hydroxyisobutyl group, 1,2-dihydroxyethyl group,1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group,1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group,2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group,1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group,1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group,2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group,1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group,1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3-tricyano-propyl group,nitromethyl group, 1-nitroethyl group, 2-nitroethyl group,2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropylgroup, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, phenylgroup, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthrylgroup, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group,3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group,1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group,4-styrylphenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group,2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group,p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group,m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group,o-tolyl group, m-tolyl group, p-tolyl group, p-t-butylphenyl group,p-(2-phenylpropyl)phenyl group, 3-methyl-2-naphthyl group,4-methyl-1-naphthyl group, 4-methyl-1-anthryl group,4′-methyl-biphenylyl group, 4″-t-butyl-p-terphenyl-4-yl group,2-pyrrolyl group, 3-pyrrolyl group, pyradinyl group, 2-pyridinyl group,3-pyridinyl group, 4-pyridinyl group, 2-indolyl group, 3-indolyl group,4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolylgroup, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furylgroup, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group,5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group,1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranylgroup, 5-isobenzofuranyl group, 6-isobenzofuranyl group,7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolylgroup, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolylgroup, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group,5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group,8-isoquinolyl group, 2-quinoxanyl group, 5-quinoxanyl group,6-quinoxanyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolylgroup, 4-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinylgroup, 3-phenanthridinyl group, 4-phenanthridinyl group,6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinylgroup, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinylgroup, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group,9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-ylgroup, 1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group,1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group,1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group,1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group,1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group,1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group,1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group,1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group,1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group,1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group,1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group,1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group,1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group,2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group,2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group,2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group,2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group,2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group,2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group,2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group,2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group,2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group,2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group,2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group,2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group,1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group,2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group,1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group,4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolylgroup, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group,2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group,2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group,2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group,3-methyl-pyrrol-2-yl group, 3-methylpyrrol-4-yl group,3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group,3-(2-phenylpropyl)pyrrol-1-yl group, 2-methyl-1-indolyl group,4methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolylgroup, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group,2-t-butyl-3-indolyl group or 4-t-butyl-3-indolyl group.

Examples of the substituted or unsubstituted alkyl groups having 1 to 30carbon atoms which are represented by R₁ and R₂ include methyl group,ethyl group, propyl group, isopropyl group, n-butyl group, s-butylgroup, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group,n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethylgroup, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethylgroup, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group,1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group,2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group,1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group,1,2,3-trichloro-propyl group, bromomethyl group, 1-bromoethyl group,2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group,1,3-dibromo-isopropyl group, 2,3-dibromo-t-butyl group,1,2,3tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triamino-propyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3tricyanopropyl group, nitromethylgroup, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group,1,2-dinitroethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butylgroup and 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted alkenyl groups having 2 to40 carbon atoms which are represented by R₁ and R₂ include vinyl group,allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group,1,3-butadienyl group, 1-methylvinyl group, styryl group,2,2-diphenylvinyl group, 2,2-ditolylvinyl group, 1,2-ditolylvinyl group,1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group,1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group,3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenylgroup and 3-phenyl-1-butenyl group.

Examples of the substituted or unsubstituted cycloalkyl groups having 5to 40 carbon atoms which are represented by R₁ and R₂ includecyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl groupand 4-methylcyclohexyl group.

The substituted or unsubstituted alkoxyl groups having 1 to 30 carbonatoms which are represented by R₁ and R₂ are represented by —OY.Examples of the group represented by Y include methyl group, ethylgroup, propyl group, isopropyl group, n-butyl group, s-butyl group,isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptylgroup, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group,2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group,1,3-dihydroxy-isopropyl group, 2,3-dihydroxy-t-butyl group,1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group,2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group,1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group,1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group,2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group,1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group,1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triamino-propyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3tricyanopropyl group, nitromethylgroup, 1-nitroethyl group, 2-nitroethyl group, 2-nitroisobutyl group,1,2-dinitro-ethyl group, 1,3-dinitroisopropyl group, 2,3-dinitro-t-butylgroup and 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted aromatic hydrocarbon groupshaving 5 to 40 carbon atoms which are represented by R₁ and R₂ includephenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group,2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthrylgroup, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group,1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group,1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group,3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group,p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group,m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolylgroup, p-tolyl group, p-t-butylphenyl group, p-(2-phenylpropyl)phenylgroup, 3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group,4-methyl-1-anthryl group, 4′-methylbiphenylyl group and4″-t-butyl-p-terphenyl-4-yl group.

Examples of the substituted or unsubstituted aromatic heterocyclicgroups having 2 to 40 carbon atoms which are represented by R₁ and R₂include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyradinylgroup, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group,1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group,5-indolyl group, 6-indolyl group, 7-indolyl group, 1 isoindolyl group,2-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolylgroup, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furylgroup, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group,5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group,1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranylgroup, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group,5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group,1 isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group,5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group,8-isoquinolyl group, 2-quinoxanyl group, 5-quinoxanyl group,6-quinoxanyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolylgroup, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group,2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinylgroup, 6-phenanthridinyl group, 7-phenanthridinyl group,8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinylgroup, 1-acridinyl group, 2-acridinyl group, 3-acridinyl group,4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group,1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin-4-yl group,1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group,1,7-phenanthrolin-8-yl group, 1,7-phenanthrolin-9-yl group,1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group,1,8-phenanthrolin-3-yl group, 1,8-phenanthrolin-4-yl group,1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group,1,8-phenanthrolin-7-yl group, 1,8-phenanthrolin-9-yl group,1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl group,1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group,1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group,1,9-phenanthrolin-7-yl group, 1,9-phenanthrolin-8-yl group,1,9-phenanthrolin-10-yl group, 1,10-phenanthrolin-2-yl group,1,10-phenanthrolin-3-yl group, 1,10-phenanthrolin-4-yl group,1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group,2,9-phenanthrolin-3-yl group, 2,9-phenanthrolin-4-yl group,2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group,2,9-phenanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group,2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group,2,8-phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group,2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group,2,8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group,2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group,2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group,2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group,2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group,2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group,1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group,4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group,2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group,10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolylgroup, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group,2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group,2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group,2-methyl-pyrrol-5-yl group, 3-methylpyrrol-1-yl group,3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group,3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group,3-(2-phenylpropyl)pyrrol-1-yl group, 2-methyl-1-indolyl group,4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolylgroup, 2-t-butyl-1-indolyl group, 4-t-butyl-1-indolyl group,2-t-butyl-3-indolyl group and 4-t-butyl-3-indolyl group.

Examples of the substituted or unsubstituted aralkyl groups having 7 to40 carbon atoms which are represented by R₁ and R₂ include benzyl group,1-phenylethyl group, 2-phenylethyl group, 1-phenyl isopropyl group,2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group,1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropylgroup, 2-α-naphthylisopropyl group, β-naphthylmethyl group,1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropylgroup, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group,2-(1-pyrrolyl)ethyl group, p-methylbenzyl group, m-methylbenzyl group,o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group,o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group,o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group,o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group,o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group,o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group,o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group,o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group and1-chloro-2-phenylisopropyl group.

The substituted or unsubstituted aryloxyl groups having 6 to 40 carbonatoms which are represented by R₁ and R₂ are represented by —OZ.Examples of the group represented by Z include phenyl group, 1-naphthylgroup, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthrylgroup, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group,4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group,2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenylgroup, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group,4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group,p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group,m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group,p-t-butylphenyl group, p-(2-phenylpropyl)phenyl group,3-methyl-2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthrylgroup, 4′-methylbiphenylyl group, 4″-t-butyl p-terphenyl-4-yl group,2-pyrrolyl group, 3-pyrrolyl group, pyradinyl group, 2-pyridinyl group,3-pyridinyl group, 4-pyridinyl group, 2-indolyl group, 3-indolyl group,4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group,1-isoindolyl group, 3-isoindolyl group, 4-isoindolyl group, 5-isoindolylgroup, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group; 3-furylgroup, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group,5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group,1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranylgroup, 5-isobenzofuranyl group, 6-isobenzofuranyl group,7-isobenzo-furanyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolylgroup, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolylgroup, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group,5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group,8-isoquinolyl group, 2-quinoxanyl group, 5-quinoxanyl group,6-quinoxanyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolylgroup, 4-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinylgroup, 3-phenanthridinyl group, 4-phenanthridinyl group,6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinylgroup, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinylgroup, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group,9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-ylgroup, 1,7-phenanthrolin-4-yl group, 1,7-phenanthrolin-5-yl group,1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group,1,7-phenanthrolin-9-yl group, 1,7-phenanthrolin-10-yl group,1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group,1,8-phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group,1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group,1,8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group,1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group,1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group,1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-'7-yl group,1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group,1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3-yl group,1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group,2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin-3-yl group,2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group,2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-7-yl group,2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group,2,8-phenanthrolin-1-yl group, 2,8-phenanthrolin-3-yl group,2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group,2,8-phenanthrolin-6-yl group, 2,8-phenanthrolin-7-yl group,2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group,2,7-phenanthrolin-1-yl group, 2,7-phenanthrolin-3-yl group,2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group,2,7-phenanthrolin-6-yl group, 2,7-phenanthrolin-8-yl group,2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group,1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group,2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group,1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group,4-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolylgroup, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group,2-thienyl group, 3-thienyl group, 2-methylpyrrol-1-yl group,2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group,2-methyl-pyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methylpyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group,2-t-butylpyrrol-4-yl group, 3-(2-phenylpropyl)pyrrol-1-yl group,2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolylgroup, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group,4-t-butyl-1-indolyl group, 2-t-butyl-3-indolyl group and4-t-butyl-3-indolyl group.

The substituted or unsubstituted alkoxycarbonyl groups having 2 to 30carbon atoms which are represented by R₁ and R₂ are represented by—COOY. Examples of the group represented by Y include methyl group,ethyl group, propyl group, isopropyl group, n-butyl group, s-butylgroup, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group,n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethylgroup, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethylgroup, 1,3-dihydroxy-isopropyl group, 2,3-dihydroxy-t-butyl group,1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group,2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group,1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group,1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group,2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group,1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group,1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group,2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group,1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropylgroup, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group,2-aminoisobutyl group, 1,2-diaminoethyl group, 1,3-diaminoisopropylgroup, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group,cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group,2-cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropylgroup, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group,nitromethyl group, 1-nitroethyl group, 2-nitroethyl group,2-nitroisobutyl group, 1,2-dinitroethyl group, 1,3-dinitroisopropylgroup, 2,3-dinitro-t-butyl group and 1,2,3-trinitropropyl group.

Examples of the substituted or unsubstituted silyl groups having 3 to 40carbon atoms which are represented by R₁ and R₂ include trialkylsilylgroups such as trimethylsilyl group, triethylsilyl group, tripropylsilylgroup, tributylsilyl group, tripentylsilyl group, trihexylsilyl groupand t-butyldimethylsilyl group, dialkylarylsilyl groups,alkyldiarylsilyl groups and triarylsilyl groups. Examples of the alkylgroup and the aryl group include the same groups as those describedabove.

When the groups represented by Ar₁ and Ar₂ or the groups represented byR₁ and R₂ each independently are bonded to each other and form a cyclicstructure, examples of the formed structures include the followingstructures:

In the foregoing general formula (B), A′ represents a group which isselected from groups represented by general formulae (2) to (12):

In general formulae (2) to (12), Ar₁ to Ar₃ each independently representa substituted or unsubstituted aryl group having 6 to 30 carbon atoms,Ar₄ represents a substituted or unsubstituted arylene group having 6 to30 carbon atoms, Ar₅ represents a substituted or unsubstituted trivalentaromatic residue group having 6 to 30 carbon atoms, and R₁ and R₂ eachindependently represent hydrogen atom, a halogen atom, hydroxyl group, asubstituted or unsubstituted amino group, nitro group, cyano group, asubstituted or unsubstituted alkyl group having 1 to 30 carbon atoms, asubstituted or unsubstituted alkenyl group having 2 to 40 carbon atoms,a substituted or unsubstituted cycloalkyl group having 5 to 40 carbonatoms, a substituted or unsubstituted alkoxyl group having 1 to 30carbon atoms, a substituted or unsubstituted aromatic hydrocarbon grouphaving 5 to 40 carbon atoms, a substituted or unsubstituted aromaticheterocyclic group having 2 to 40 carbon atoms, a substituted orunsubstituted aralkyl group having 7 to 40 carbon atoms, a substitutedor unsubstituted aryloxyl group having 6 to 40 carbon atoms, asubstituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbonatoms, a substituted or unsubstituted silyl group having 3 to 40 carbonatoms or carboxyl group. Groups represented by Ar₁ and Ar₂ and groupsrepresented by R₁ and R₂ each independently may be bonded to each otherand form a cyclic structure. p in general formula (12) represents 0 or1.

The foregoing general formulae (2) to (12) may be substituted withsubstituted or unsubstituted alkyl groups having 1 to 30 carbon atoms orsubstituted or unsubstituted phenyl group, and in the foregoing generalformula (B), A′ does not represent phenyl group substituted with anarylamino group when the group represented by B is substituted with anarylamino group.

Examples of the atoms and groups represented by Ar₁ to Ar₅, R₁ and R₂include the atoms and groups described as the examples of the atoms andgroups represented by Ar₁ to Ar₅, R₁ and R₂ in the foregoing generalformulae (1) to (11) in general formula (A).

Examples of the substituent in the groups in general formulae (A) and(B) include halogen atoms, hydroxyl group, substituted or unsubstitutedamino groups, nitro group, cyano group, substituted or unsubstitutedalkyl groups, substituted or unsubstituted alkenyl groups, substitutedor unsubstituted cycloalkyl groups, substituted or unsubstituted alkoxylgroups, substituted or unsubstituted aromatic hydrocarbon groups,substituted or unsubstituted aromatic heterocyclic groups, substitutedor unsubstituted aralkyl groups, substituted or unsubstituted aryloxylgroups, substituted or unsubstituted alkoxycarbonyl groups and carboxylgroup.

It is preferable that the groups represented by general formulae (1) to(11) in general formula (A) and groups represented by general formulae(2) to (12) in general formula (B) are each independently substitutedwith an alkyl group having 1 to 30 carbon atoms or a cycloalkyl groupshaving 5 to 30 carbon atoms.

Examples of the novel aromatic compound represented by general formula(A) or (B) are shown in the following. However, the novel compound isnot limited to the compounds shown as the examples.

It is preferable that the above aromatic compound represented by generalformula (A) or (B) of the present invention is used as a material fororganic EL devices.

The organic EL device of the present invention comprises a cathode, ananode and an organic thin film layer comprising at least one layercontaining a light emitting layer and sandwiched between the cathode andthe anode, wherein at least one layer in the organic thin film layercomprises the aromatic compound represented by general formula (A) or(B) singly or as a component of a mixture.

It is preferable that the organic thin film layer comprises at least oneof an electron transporting layer and a hole transporting layer, and atleast one of the electron transporting layer and the hole transportinglayer comprises the aromatic compound represented by general formula (A)or (B) singly or as a component of a mixture.

It is preferable that the light emitting layer further comprises anarylamine compound and/or a styrylamine compound.

As the arylamine compound, arylamine compounds represented by thefollowing general formula (C) are preferable.

wherein Ar₆ represents an aromatic group having 6 to 40 carbon atoms,Ar₇ and Ar₈ each independently represent hydrogen atom or an aromaticgroup having 6 to 20 carbon atoms, and m represents an integer of 1 to4.

Examples of the aromatic group having 6 to 40 carbon atoms which isrepresented by Ar₆ include aryl groups having 6 to 40 carbon atoms suchas phenyl group, naphthyl group, anthranyl group, phenanthryl group,pyrenyl group, coronyl group, biphenyl group, terphenyl group, pyrrolylgroup, furanyl group, thiophenyl group, benzothiophenyl group,oxadiazolyl group, diphenylanthranyl group, indolyl group, carbazolylgroup, pyridyl group, benzoquinolyl group, fluoranthenyl group andacenaphthofluoranthenyl group; and arylene groups having 6 to 40 carbonatoms such as phenylene group, naphthylene group, anthranylene group,phenanthrylene group, pyrenylene group, coronylene group, biphenylenegroup, terphenylene group, pyrrolylene group, furanylene group,thiophenylene group, benzothiophenylene group, oxadiazolylene group,diphenylanthranylene group, indolylene group, carbazolylene group,pyridylene group, benzoquinolylene group, fluoranthenylene group andacenaphtho fluoranthenylene group.

The aromatic group having 6 to 40 carbon atoms may be substituted withsubstituents. Examples of the substituent include alkyl groups having 1to 6 carbon atoms such as ethyl group, methyl group, i-propyl group,n-propyl group, s-butyl group, t-butyl group, pentyl group, hexyl group,cyclopentyl group and cyclohexyl group; alkoxyl groups having 1 to 6carbon atoms such as ethoxyl group, methoxyl group, i-propoxyl group,n-propoxyl group, s-butoxyl group, t-butoxyl group, pentoxyl group,hexyloxyl group, cyclopentoxyl group and cyclohexyloxyl group; arylgroups having nuclei having 5 to 40 atoms; amino groups substituted withan aryl group having nuclei having 5 to 40 atoms; ester groups having anaryl group having nuclei having 5 to 40 atoms; ester groups having analkyl group having 1 to 6 carbon atoms; cyano group; nitro group; andhalogen atoms.

Examples of the aromatic group having 6 to 20 carbon atoms which isrepresented by Ar₇ or Ar₈ include the compounds having 6 to 20 carbonatoms among the compounds having 6 to 40 carbon atoms which arerepresented by Ar₈.

Examples of the above arylamine compound include triphenylamine,diphenylnaphthylamine and diphenylpyrenylamine.

As the styrylamine compound, styrylamine compounds represented by thefollowing general formula (D) are preferable:

wherein Ar₉ represents a divalent group selected from phenylene group,terphenylene group, stilbene group and distyrylarylene groups, Ar₁₀ andAr₁₁ each independently represent hydrogen atom or an aromatic grouphaving 6 to 30 carbon atoms, the groups represented by Ar₉, Ar₁₀ or Ar₁₁may be substituted, at least one of the groups represented by Ar₁₀ andAr₁₁ is substituted with styryl group, and n represents an integer of 1to 4.

Examples of the substituent to the groups represented by Ar₉, Ar₁₀ andAr₁₁ include the above substituents to the groups represented by Ar₆ ingeneral formula (C).

Examples of the organic EL device of the present invention includeorganic EL devices having a laminate structure having one or moreorganic layers laminated between the electrodes. Examples of thestructure include structures of an anode/a light emitting layer/acathode, an anode/a hole transporting layer/a light emitting layer/anelectron transporting layer/a cathode, an anode/a hole transportinglayer/a light emitting layer/a cathode and an anode/a light emittinglayer/an electron transporting layer/a cathode. The aromatic compound ofthe present invention may be used in any of the layers in the aboveorganic thin film layer and may also be used by doping other holetransporting materials, light emitting materials and electrontransporting materials.

In the organic EL device of the present invention, it is preferable thata region transporting electrons or an interface region between thecathode and a layer of an organic thin film comprises a reducing dopant.The reducing dopant is defined as a substance which can reduce theelectron transporting compound. Therefore, various types of substancescan be used as long as the substance has the specific reducing property.For example, at least one substance selected from the group consistingof alkali metals, alkaline earth metals, rare earth metals, oxides ofalkali metals, halides of alkali metals, oxides of alkaline earthmetals, halides of alkaline earth metals, oxides of rare earth metals,halides of rare earth metals, organic complexes of alkali metals,organic complexes of alkaline earth metals and organic complexes of rareearth metals, can be used.

Specific examples of the reducing dopant include at least one alkalimetal selected from the group consisting of Na (the work function: 2.36eV), K (the work function: 2.28 eV), Rb (the work function: 2.16 eV) andCs (the work function: 1.95 eV) and at least one alkaline earth metalselected from the group consisting of Ca (the work function: 2.9 eV), Sr(the work function: 2.0 to 2.5 eV) and Ba (the work function: 2.52 eV).Among these reducing dopants, reducing dopants having a work function of2.9 eV or smaller are preferable. It is more preferable that thereducing dopant is at least one alkali metal selected from the groupconsisting of K, Rb and Cs, still more preferably Rb or Cs, and mostpreferably Cs. These alkali metals have particularly great reducingability, and the luminance of emitted light and the life of the organicEL device are improved by adding these alkali metals in a relativelysmall amount into the region of electron injection. As the reducingdopant having a work function of 2.9 eV or smaller, combinations of twoor more alkali metals are also preferable, and combinations including Cssuch as combinations of Cs and Na, Cs and K, Cs and Rb, and Cs, Na and Kare more preferable. When Cs is include in the combination, the reducingability can be efficiently exhibited, and the luminance of emitted lightand the life of the organic EL device can be improved by adding thecombination into the region of electron injection.

The organic EL device of the present invention may further comprises anelectron injecting layer constituted with an insulating material or asemiconductor and disposed between the cathode and the organic thin filmlayer. Due to the electron injecting layer, leak of electric current canbe effectively prevented, and the electron injecting property can beimproved. It is preferable that at least one metal compound selectedfrom the group consisting of alkali metal chalcogenides, alkaline earthmetal chalcogenides, alkali metal halides and alkaline earth metalhalides is used as the insulating material. It is preferable that theelectron injecting layer is constituted with the alkali metalchalcogenide or the like material since the electron injecting propertycan be further improved. Examples of the alkali metal chalcogenideinclude Li₂O, LiO, Na₂S, Na₂Se and NaO. Preferable examples of thealkaline earth metal chalcogenide include CaO, BaO, SrO, BeO, BaS andCaSe. Examples of the alkali metal halide include LiF, NaF, KF, LiCl,KCl and NaCl. Examples of the alkaline earth metal halide includefluorides such as CaF₂, BaF₂, SrF₂, MgF₂ and BeF₂ and halides other thanthe fluorides.

Examples of the semiconductor constituting the electron transportinglayer include oxides, nitrides and oxide nitrides containing at leastone element selected from Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg,Si, Ta, Sb and Zn, which are used singly or as a combination of two ormore. It is preferable that the inorganic compound constituting theelectron transporting layer is in the form of a fine crystalline oramorphous insulating thin film. When the electron transporting layer isconstituted with the above insulating thin film, a more uniform thinfilm can be formed and defective pixels such as dark spots can bedecreased. Examples of the inorganic compound include the alkali metalchalcogenides, the alkaline earth metal chalcogenides, the alkali metalhalides and the alkaline earth metal halides which are described above.

The anode of the organic EL device plays the role of injecting holesinto the hole transporting layer or the light emitting layer. It iseffective that the anode has a work function of 4.5 eV or greater.Examples of the material of the anode used in the present inventioninclude indium tin oxide alloys (ITO), tin oxides (NESA), gold, silver,platinum and copper. As the cathode, a material having a small workfunction is preferable so that electrons can be injected into theelectron transporting layer or the light emitting layer.

The process for forming the layers in the organic EL device of thepresent invention is not particularly limited. A conventional processsuch as the vacuum vapor deposition process and the spin coating processcan be used. The organic thin film layer comprising the compoundrepresented by the above general formula (A) or (B) can be formed inaccordance with the vacuum vapor deposition process, the molecular beamepitaxy process (the MBE process) or, using a solution prepared bydissolving the compound into a solvent, in accordance with aconventional coating process such as the clipping process, the spincoating process, the casting process, the bar coating process and theroll coating process.

The thickness of each layer in the organic thin film layer in theorganic EL device of the present invention is not particularly limited.In general, an excessively thin layer tends to have defects such as pinholes, and an excessively thick layer requires a high applied voltage todecrease the efficiency. Therefore, a thickness in the range of severalnm to 1 μm is preferable.

As described above, by using the novel aromatic compound of the presentinvention for the organic thin film layer of the organic EL device ofthe present invention, the organic EL device which exhibits a greatluminance of emitted light, a great efficiency of light emission and ahigh purity of color, emits bluish light, is excellent in stability athigh temperatures and has a long life can be obtained. This organic ELdevice can be advantageously used for a photosensitive member forelectronic photograph, a planar light emitting member such as a flatpanel display of wall televisions, a back light of copiers, printers andliquid crystal displays, a light source for instruments, a displaypanel, a marking light and an accessory.

The present invention will be described more specifically with referenceto examples in the following. However, the present invention is notlimited to the examples.

Synthesis Example 1 Synthesis of Compound (A1) (1) Synthesis of9-(2-naphthyl)anthracene

Under an atmosphere of argon, 9-bromoanthracene (3 g, 12 mmole),2-naphthaleneboric acid (2.4 g, 14 mmole, 1.2 eq) andtetrakis-(triphenylphosphine)palladium(0) (0.28 g, 0.24 mmole, 2% Pd)were suspended in dimethoxyethane (40 ml). To the obtained suspension, a2M aqueous solution of sodium carbonate (4.5 g, 42 mmole, 3 eq/20 ml)was added, and the resultant mixture was refluxed for 10 hours. Theobtained reaction mixture was filtered and washed with water andmethanol, and a light yellow solid substance was obtained. The solidsubstance was suspended in boiling dimethoxy-ethane (30 ml), cooledwhile being left standing, filtered and washed with dimethoxyethane andacetone, and a gray solid substance (82% crude) was obtained. This solidsubstance was purified using a short column (silica gel/dichloroethane),and a light yellow solid substance (2.7 g, the yield: 74%) was obtained.The obtained product was identified to be 9-(2-naphthyl)anthracene inaccordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 7.2-7.7 (9H, m), 7.8-8.1 (6H, m), 8.51 (1H, s).

(2) Synthesis of 9-bromo-10-(2-naphthyl)anthracene

9-(2-Naphthyl)anthracene (2.7 g, 8.9 mmole) was suspended in anhydrousN,N-dimethylformamide (DMF) (50 ml). To the obtained suspension, ananhydrous DMF solution (6 ml) of N-bromosuccinimide (NBS) (1.7 g, 9.6ml, 1.1 eq) was added, and the resultant mixture was stirred at the roomtemperature for 10 hours and then left standing for one night. Thereaction mixture was diluted with water (50 ml). The formed solidsubstance was separated by filtration and washed with methanol, and alight yellow solid substance (3.2 g, the yield: 94%) was obtained. Theobtained product was identified to be 9-bromo-10-(2-naphthyl)anthracenein accordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 7.2-7.7 (9H, m), 7.8-8.1 (4H, m), 8.62 (2H, d,J=8 Hz).

(3) Synthesis of9-(4-(2,2-diphenylvinyl)phenyl)-10-(2-naphthyl)-anthracene (Compound(A1))

Under an atmosphere of argon, 9-bromo-10-(2-naphthyl)anthracene (3.2 g,8.4 mmole), 4-(2,2diphenylvinyl)phenylboric acid (2.8 g, 9.3 mmole, 1.1eq) and tetrakis(triphenylphosphine)palladium(0) (0.19 g, 0.16 mmole, 2%Pd) were suspended in toluene (30 ml). To the obtained suspension, a 2Maqueous solution of sodium carbonate (3 g, 28 mmole, 3 eq/15 ml) wasadded, and the resultant mixture was refluxed for 10 hours. The obtainedreaction mixture was filtered and washed with toluene, water andmethanol, and a light yellow solid substance (3.7 g) was obtained. Thesolid substance was suspended in boiling toluene (40 ml), cooled whilebeing left standing and filtered, and a light yellow solid substance(3.4 g, the yield: 73%) was obtained. The result of examination of theobtained product in accordance with ¹H-NMR was as follows:

¹H-NMR (CDCl₃, TMS) δ: 7.15 (1H, s), 7.2-7.4 (17H, m), 7.5-7.8 (8H, m),7.8-8.1 (4H, m).

The obtained solid substance (3.4 g) was purified by sublimation at 340°C./10⁻⁶ Torr for 1 hour, and a light yellow substance (2.9 g) wasobtained. It was confirmed in accordance with the field desorption massanalysis (FDMS) that the obtained product was the object compound(Compound (A1)). The results of measurements of the energy gap Eg, theionization potential Ip and the glass transition temperature Tg are alsoshown in the following.

FDMS: calcd. for C₄₄H₃₀=558, found m/z=558 (M+, 100)

λmax: 397, 378, 359 nm (PhMe)

Fmax: 438 nm (PhMe: λex=397 nm)

Ip=5.71 eV (100 nW, 27 Y/eV)

Tg=108° C.

Synthesis Example 2 Synthesis of Compound (A2) (1) Synthesis of9-(3,5-dibromophenyl)anthracene

Under an atmosphere of argon, 9-iodoanthracene (8.7 g, 29 mmole, 1.1eq), 3,5-dibromophenylboric acid (7.3 g, 26 mmole) andtetrakis-(triphenylphosphine)palladium(0) (0.67 g, 0.58 mmole, 2% Pd)were suspended in toluene (80 ml). To the obtained suspension, a 2Maqueous solution of sodium carbonate (8.3 g, 78 mmole, 3 eq/40 ml) wasadded, and the resultant mixture was refluxed for 10 hours. An organiclayer was separated from the obtained reaction mixture, washed with asaturated aqueous solution of sodium chloride and dried with magnesiumsulfate. After the solvent was removed by distillation, a yellow solidsubstance was obtained and, then, the obtained solid substance wassuspended in dichloromethane (20 ml). The solid component was separatedby filtration and washed with a mixed solution of dichloromethane andhexane, and a light yellow solid substance (5.1 g, the yield: 48%, thefirst crop) was obtained. The filtrate was purified in accordance withthe column chromatography (silica gel/hexane, hexane+5%dichloromethane), and a light yellow solid substance (4.2 g, the yield:39%, the second crop) was obtained. The yellow solid substances of thefirst crop and the second crop were combined (9.3 g, the yield: 87%).The obtained product was identified to be9-(3,5-dibromophenyl)anthracene in accordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 7.3-7.6 (8H, m), 7.85 (1H, t, J=2 Hz), 8.0-8.1(2H, m), 8.49 (1H, s).

(2) Synthesis of 9-(3,5-diphenylphenyl)anthracene

Under an atmosphere of argon, 9-(3,5-dibromophenyl)anthracene (5 g, 12mmole), phenylboric acid (4.4 g, 36 mmole, 3 eq) andtetrakis(triphenylphosphine)palladium(0) (0.55 g, 0.48 mmole, 2% Pd)were dissolved in toluene (100 ml). To the obtained solution, a 2Maqueous solution of sodium carbonate (11 g, 0.10 moles, 3 eq/50 ml) wasadded, and the resultant mixture was refluxed for 10 hours. The obtainedreaction mixture was filtered, and an organic layer was separated fromthe filtrate, washed with a saturated aqueous solution of sodiumchloride (50 ml) and dried with magnesium sulfate. After the solvent wasremoved by distillation, a black oily substance was obtained. Theobtained oily substance was purified in accordance with the columnchromatography (silica gellhexane, hexane+3% dichloromethane, hexane+10%dichloromethane in the final step), and a light yellow amorphous solidsubstance (3.6 g, 74%) was obtained. The obtained product was identifiedto be 9-(3,5-diphenyl-phenyl)anthracene in accordance with ¹H-NMR andFDMS.

¹H-NMR (CDCl₃, TMS) δ: 7.3-7.6 (10H, m), (1H, s), 7.7-7.9 (8H, m), 8.01(1H, s), 8.05 (2H, dd, J=9 Hz, 2 Hz), 8.52 (1H, s).

FDMS: calcd. for C₃₂H₂₂=406, found m/z=406 (M+, 100)

(3) Synthesis of 9-bromo-10-(3,5-diphenylphenyl)anthracene

9-(3,5-Diphenylphenyl)anthracene (3.6 g, 8.9 mmole) was suspended inanhydrous DMF (60 ml). After an anhydrous DMF solution (7 ml) of NBS(1.9 g, 11 mmole, 1.2 eq) was added, the resultant mixture was stirredat the room temperature for 10 hours and then left standing for onenight. The reaction mixture was diluted with water (50 ml). The formedsolid substance was separated by filtration and washed with methanol,and a light yellow solid substance (3.9 g, the yield: 90%) was obtained.The obtained product was identified to be9-bromo-10-(3,5-diphenylphenyl)anthracene in accordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 7.3-7.9 (18H, m), 8.01 (1H, t, J=2 Hz), 8.62 (2H,d, J=9 Hz).

(4) Synthesis of9-(4-(2,2-diphenylvinyl)phenyl)-10-(3,5-diphenylphenyl)-anthracene(Synthesis of Compound (A2))

Under an atmosphere of argon, 9-bromo-10-(3,5-diphenylphenyl)-anthracene(3.9 g, 8.0 mmole), 4-(2,2-diphenylvinyl)phenylboric acid (2.7 g, 9.0mmole, 1.1 eq) and tetrakis(triphenylphosphine)palladium(0) (0.18 g,0.16 mmole, 2% Pd) were suspended in toluene (30 ml). To the obtainedsuspension, a 2M aqueous solution of sodium carbonate (2.9 g, 27 mmole,3 eq/15 ml) was added, and the resultant mixture was refluxed for 10hours. An organic layer was separated from the reaction mixture, washedwith a saturated aqueous solution of sodium chloride (30 ml) and driedwith magnesium sulfate. After the solvent was removed by distillation, abrown solid substance was obtained. The obtained solid substance waspurified in accordance with the column chromatography (silicagel/hexane+10% dichloromethane, hexane+20% dichloromethane), and a whitesolid substance (4.3 g, the yield: 81%) was obtained. The result ofexamination of the obtained product in accordance with ¹H-NMR was asfollows:

¹H-NMR (CDCl₃, TMS) δ: 7.15 (1H, s), 7.2-7.5 (24H, m), 7.7-7.9 (10H, m),8.02 (1H, t, J=2 Hz).

The obtained solid substance (4.3 g) was purified by sublimation at 360°C./10⁻⁶ Torr for 1 hour, and a light yellow substance (3.2 g) wasobtained. It was confirmed in accordance with FDMS that the obtainedproduct was the object compound (Compound (A2)). The results ofmeasurements of Eg, Ip and Tg are also shown in the following.

FDMS: calcd. for C₅₂H₃₀=660, found m/z=660 (M+, 100)

λmax: 397, 377, 359 nm (PhMe)

Fmax: 435 nm (PhMe: λex=397 nm)

Ip=5.82 eV (100 nW, 27 Y/eV)

Tg=120° C.

Synthesis Example 3 Synthesis of Compound (A3) (1) Synthesis of9-(3,4-dichlorophenyl)anthracene

Under an atmosphere of argon, 3,4-dichlorophenylboric acid (2.7 g, 14mmole, 1.1 eq), 9-bromoanthracene (3.3 g, 13 mmole) andtetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.26 mmole, 2% Pd) weresuspended in toluene (40 ml). To the obtained suspension, a 2M aqueoussolution of sodium carbonate (4.5 g, 42 mmole, 3 eq/20 ml) was added,and the resultant mixture was refluxed for 10 hours. The reactionmixture was filtered to remove Pd black, and an organic layer wasseparated from the filtrate, washed with a saturated aqueous solution ofsodium chloride (30 ml) and dried with magnesium sulfate. After thesolvent was removed by distillation, a light brown oily substance wasobtained. When a small amount of methanol was added to the obtained oilysubstance and the wall of the flask was rubbed, crystals were formed.The formed crystals were separated by filtration and washed withmethanol, and a light yellow solid substance (3.7 g, the yield: 88%) wasobtained. The obtained product was identified to be9-(3,4-dichlorophenyl)anthracene in accordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 7.2-7.7 (9H, m), 8.02 (2H, dd, J=7 Hz, 2 Hz),8.48 (1H, s).

(2) Synthesis of 9-(3,4-diphenylphenyl)anthracene

Under an atmosphere of argon, phenylboric acid (3.6 g, 30 mmole, 2.7eq), 9-(3,4-dichlorophenyl)anthracene (3.7 g, 11 mmole) anddichlorobis(triphenylphosphine)nickel(II) (0.72 g, 1.1 mmole, 5% Ni),triphenylphosphine (0.58 g, 2.2 mmole, 2 eq to Ni) and potassiumphosphate hydrate (16 g, 60 mmole, 2 eq) were suspended in anhydroustoluene (80 ml), and the obtained suspension was heated at 80° C. for 10hours. To the reaction mixture, water (50 ml) was added, and insolublecomponents were removed by filtration. An organic layer was separatedfrom the filtrate, washed with a saturated aqueous solution of sodiumchloride (30 ml) and dried with magnesium sulfate. After the solvent wasremoved by distillation, a light brown oily substance was obtained. Theobtained oily substance was purified in accordance with the columnchromatography (silica gel/hexane+10% dichloromethane, hexane+20%dichloromethane, hexane+30% dichloromethane in the final step), and awhite solid substance (3.7 g, the yield: 83%) was obtained. The obtainedproduct was identified to be 9-(3,4-diphenylphenyl)anthracene inaccordance with ¹H-NMR and FDMS.

¹H-NMR (CDCl₃, TMS) δ: 7.1-7.7 (17H, m), 7.8-8.1 (4H, m), 8.49 (1H, s).

FDMS: calcd. for C₃₂H₂₂=406, found m/z=406 (M+, 100).

(3) Synthesis of (3,4-diphenylphenyl)-10-bromoanthracene

9-(3,4-Diphenylphenyl)anthracene (3.7 g, 9.1 mmole) was suspended inanhydrous DMF (50 ml). After an anhydrous DMF solution (10 ml) of NBS(1.8 g, 10 mmole, 1.1 eq) was added, the resultant mixture was heated at55° C. for 5 minutes so that the reaction mixture became a homogeneoussolution. The obtained solution was stirred at the room temperature for4 hours and then left standing for one night. The reaction mixture wasdiluted with water (50 ml). The formed solid substance was separated byfiltration and washed with methanol, and a light yellow solid substance(4.2 g, the yield: 95%) was obtained. The obtained product wasidentified to be 9-(3,4-diphenylphenyl)-10-bromo-anthracene inaccordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) 6.2-7.7 (17H, m), 7.85 (2H, d, J=8 Hz), 8.61 (2H, d,J=8 Hz).

(4) Synthesis of9-(3,4-diphenylphenyl)-10-(4-(2,2-diphenylvinyl)phenyl)-anthracene(Synthesis of Compound (A3))

Under an atmosphere of argon, 9-(3,4-diphenylphenyl)-10-bromo-anthracene(3.0 g, 6.2 mmole), 4-(2,2-diphenylvinyl)phenylboric acid (2.0 g, 6.7mmole, 1.1 eq) and tetrakis(triphenylphosphine)palladium(0) (0.14 g,0.12 mmole, 2% Pd) were suspended in toluene (20 ml). To the obtainedsuspension, a 2M aqueous solution of sodium carbonate (2.1 g, 20 mmole,3 eq/10 ml) was added, and the resultant mixture was refluxed for 10hours. The reaction mixture was filtered and washed with water andmethanol, and a light yellow solid substance (3.7 g) was obtained. Theobtained solid substance was suspended in boiling toluene (40 ml). Afterthe suspension was cooled while being left standing, the suspension wasfiltered, and a light yellow solid substance (3.6 g, the yield: 88%) wasobtained. The result of examination of the obtained product inaccordance with ¹H-NMR was as follows:

¹H-NMR (CDCl₃, TMS) δ: 0.0-7.9 (36H, m), all-H.

The obtained solid substance (3.6 g) was purified by sublimation at 340°C./10⁻⁶ Torr for 1 hour, and a light yellow solid substance (2.1 g) wasobtained. It was confirmed in accordance with FDMS that the obtainedproduct was the object compound (Compound (A3)). The results ofmeasurements of Eg, Ip and Tg are also shown in the following.

FDMS: calcd. for C₅₂H₃₆=660, found m/z=660 (M+, 100)

λmax: 398, 378, 359 nm (PhMe)

Fmax: 437 nm (PhMe: Xex=398 nm)

Ip=5.82 eV (100 nW, 64 Y/eV)

Tg=122° C.

Synthesis Example 4 Synthesis of Compound (A4) (1) Synthesis of9-(3-chlorophenyl)anthracene

Under an atmosphere of argon, 3-chlorophenylboric acid (3.3 g, 21 mmole,1.1 eq), 9-bromoanthracene (5.0 g, 19 mmole) andtetrakis-(triphenylphosphine)palladium(0) (0.5 g, 0.43 mmole, 2% Pd)were suspended in toluene (60 ml). To the obtained suspension, a 2Maqueous solution of sodium carbonate (6.8 g, 64 mmole, 3 eq/35 ml) wasadded, and the resultant mixture was refluxed for 10 hours. An organiclayer was separated from the filtrate, washed with a saturated aqueoussolution of sodium chloride (30 ml) and dried with magnesium sulfate.After the solvent was removed by distillation, a yellow oily substancewas obtained. The obtained oily substance was purified in accordancewith the column chromatography (silica gel/hexane+5% dichloromethane),and a light yellow solid substance (5.2 g, the yield: 95%) was obtained.The obtained product was identified to be 9-(3-chlorophenyl)anthracenein accordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 2-7.7 (10H, m), 7.7-7.8 (2H, m), 8.48 (1H, s).

(2) Synthesis of 9-(3-(4-phenylphenyl)phenyl)anthracene

Under an atmosphere of argon, 4-biphenylboric acid (3.6 g, 18 mmole, 1.3eq), 9-(3-chlorophenyl)anthracene (4.1 g, 14 mmole),dichloro(1,1′-bis(diphenylphosphino)ferrocene)nickel(II) (0.3 g, 0.44mmole, 3% Ni) and anhydrous potassium phosphate (10 g, 47 mmole, 2.7 eq)were suspended in anhydrous dioxane (70 ml), and the obtained suspensionwas heated at 90° C. for 7 hours. To the reaction mixture, water (50 ml)and toluene (100 ml) were added. An organic layer was separated, washedwith a saturated aqueous solution of sodium chloride (30 ml) and driedwith magnesium sulfate. After the solvent was removed by distillation, alight brown solid substance was obtained. The obtained solid substancewas suspended in a boiling mixture of ethanol (50 ml) and toluene (10ml). After the resultant mixture was cooled while being left standing,the mixture was filtered and washed with ethanol, and a white solidsubstance (4.8 g, the yield: 84%) was obtained. The obtained product wasidentified to be 9-(3-(4-phenylphenyl)phenyl)anthracene in accordancewith ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 0.3-7.8 (19H, m), 8.03 (2H, d, J=7 Hz), 8.49 (1H,s).

(3) Synthesis of 9-(3-(4-phenylphenyl)phenyl)-10-bromoanthracene

9-(3-(4-Phenylphenyl)phenyl)anthracene (4.8 g, 12 mmole) was suspendedin anhydrous DMF (70 ml). After an anhydrous DMF solution (15 ml) of NBS(2.3 g, 13 mmole, 1.1 eq) was added, the resultant mixture was heated at40° C. for 15 minutes so that the reaction mixture became a homogeneoussolution. The obtained solution was stirred at the room temperature for7 hours and then left standing for one night. The reaction mixture wasdiluted with water (50 ml). The formed solid substance was separated byfiltration and washed with methanol, and a light yellow solid substance(5.2 g, the yield: 89%) was obtained. The obtained product wasidentified to be 9-(3-(4-phenylphenyl)phenyl)-10-bromoanthracene inaccordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 7.3-7.8 (19H, m), 8.61 (2H, d, J=9 Hz).

(4) Synthesis of9-(3-(4-phenylphenyl)phenyl)-10-(4-(2,2-diphenylvinyl)-phenyl)anthracene(Synthesis of Compound (A4))

Under an atmosphere of argon,9-(3-(4-phenylphenyl)phenyl)-10-bromoanthracene (3.0 g, 6.2 mmole),4-(2,2-diphenylvinyl)phenylboric acid (2.0 g, 6.7 mmole, 1.1 eq) andtetrakis(triphenylphosphine)-palladium(0) (0.14 g, 0.12 mmole, 2% Pd)were suspended in toluene (20 ml). To the obtained suspension, a 2Maqueous solution of sodium carbonate (2.1 g, 20 mmole, 3 eq/10 ml) wasadded, and the resultant mixture was refluxed for 10 hours. The reactionmixture was filtered and washed with water and methanol, and a lightyellow solid substance was obtained. The obtained solid substance wassuspended in boiling toluene (30 ml). After the suspension was cooledwhile being left standing, the suspension was filtered, and a lightyellow solid substance (3.0 g, the yield: 73%) was obtained. The resultof examination of the obtained product in accordance with ¹H-NMR was asfollows:

¹H-NMR (CDCl₃, TMS) δ: 7.15 (1H, s), 7.2-7.4 (22H, m), 7.6-7.8 (13H, m).

The obtained solid substance (3.0 g) was purified by sublimation at 340°C./10⁻⁶ Torr for 1 hour, and a light yellow solid substance (2.6 g) wasobtained. It was confirmed in accordance with FDMS that the obtainedproduct was the object compound (Compound (A4)). The results ofmeasurements of Eg, Ip and Tg are also shown in the following.

FDMS: calcd. for C₅₂H₃₆=660, found m/z=660 (M+, 100)

λmax: 397, 377, 358 nm (PhMe)

Fmax: 434 nm (PhMe: λex=397 nm)

Ip=5.83 eV (100 nW, 82 Y/eV)

Tg=115° C.

Synthesis Example 5 Synthesis of Compound (A5) (1) Synthesis of9-(4-chlorophenyl)anthracene

Under an atmosphere of argon, 4-chlorophenylboric acid (5.0 g, 32 mmole,1.1 eq), 9-bromoanthracene (7.5 g, 29 mmole) andtetrakis-(triphenylphosphine)palladium(0) (0.7 g, 0.61 mmole, 2% Pd)were suspended in toluene (100 ml). To the obtained suspension, a 2Maqueous solution of sodium carbonate (10 g, 94 mmole, 3 eq/50 ml) wasadded, and the resultant mixture was refluxed for 10 hours. The reactionmixture was filtered to remove Pd black, and an organic layer wasseparated from the filtrate, washed with a saturated aqueous solution ofsodium chloride (30 ml) and dried with magnesium sulfate. After thesolvent was removed by distillation, a white solid substance wasobtained. The obtained solid substance was suspended in boiling ethanol(50 ml). After the mixture was cooled while being left standing, themixture was filtered and washed with ethanol, and a white solidsubstance (7.7 g, the yield: 92%) was obtained. The obtained product wasidentified to be 9-(4-chlorophenyl)anthracene in accordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 7.2-7.7 (10H, m), 8.02 (2H, dd, J=7 Hz, 2 Hz),8.48 (1H, s).

(2) Synthesis of 9-(4-chlorophenyl)-10-bromoanthracene

9-(4-Chlorophenyl)anthracene (4.0 g, 14 mmole) was suspended inanhydrous DMF (60 ml). After an anhydrous DMF solution (10 ml) of NBS(2.5 g, 14 mmole, 1 eq) was added, the resultant mixture was stirred atthe room temperature for 7 hours and then left standing for one night.The reaction mixture was diluted with water (70 ml). The formed solidsubstance was separated by filtration and washed with methanol, and alight yellow solid substance (4.6 g, the yield: 89%) was obtained. Theobtained product was identified to be9-(4-chlorophenyl)-10-bromo-anthracene in accordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 7.3-7.7 (10H, m), 8.60 (2H, d, J=9 Hz).

(3) Synthesis of9-(4-chlorophenyl)-10-(4-(2,2-diphenylvinyl)phenyl)-anthracene

Under an atmosphere of argon, 9-(4-chlorophenyl)-10-bromo-anthracene(2.0 g, 5.4 mmole), 4-(2,2-diphenylvinyl)phenylboric acid (1.8 g, 6.0mmole, 1.1 eq) and tetrakis(triphenylphosphine)palladium(0) (0.12 g,0.10 mmole, 2% Pd) were suspended in toluene (20 ml). To the obtainedsuspension, a 2M aqueous solution of sodium carbonate (1.9 g, 18 mmole,3 eq/10 ml) was added, and the resultant mixture was refluxed for 10hours. The reaction mixture was filtered and washed with water andmethanol, and a light yellow solid substance (2.4 g, the yield: 82%) wasobtained. The obtained product was identified to be9-(4-chlorophenyl)-10-(4-(2,2-diphenylvinyl)phenyl)anthracene inaccordance with ¹H-NMR.

¹H-NMR (CDCl₃, TMS) δ: 7.14 (1H, s), 7.2-7.4 (20H, m), 7.5-7.7 (6H, m).

(4) Synthesis of9-(4-diphenylaminophenyl)-10-(4-(2,2-diphenylvinyl)-phenyl)anthracene(Synthesis of Compound (A5))

Under an atmosphere of argon,9-(4-chlorophenyl)-10-(4-(2,2-diphenylvinyl)phenyl)anthracene (2.4 g,4.4 mmole), diphenylamine (0.9 g, 5.3 mmole, 1.2 eq),tris(dibenzylideneacetone)dipalladium(0) (0.1 g, 0.11 mmole, 5% Pd), atoluene solution of tri-t-butylphosphine (66% by weight, 0.05 ml, 0.16mmole, 0.7 eq to Pd) and sodium t-butoxide (0.6 g, 6.3 mmole, 1.4 eq)were suspended in anhydrous toluene (20 ml). The resultant suspensionwas refluxed for 8 hours. The reaction mixture was filtered and washedwith toluene, water and methanol, and a green solid substance wasobtained. The obtained solid substance was suspended in boiling toluene(40 ml). After the suspension was cooled while being left standing, thesuspension was filtered, and a green solid substance (2.4 g, 81%) wasobtained. The result of examination of the obtained product inaccordance with ¹H-NMR was as follows:

¹H-NMR (CDCl₃, TMS) δ: 7.0-7.4 (33H, m), 7.6-7.9 (4H, m).

The obtained solid substance (2.4 g) was purified by sublimation at 360°C./10⁻⁶ Torr for 1 hour, and a light yellow solid substance (1.9 g) wasobtained. It was confirmed in accordance with FDMS that the obtainedproduct was the object compound (Compound (A5)). The results ofmeasurements of Eg, Ip and Tg are also shown in the following.

FDMS: calcd. for C₅₂H₃₇=675, found m/z=675 (M+, 100)

λmax: 398, 379, 360, 307 nm (PhMe)

Fmax: 457 nm (PhMe: Xex=398 nm)

Ip=5.73 eV (200 nW, 16 Y/eV)

Tg=114° C.

Synthesis Example 6 Synthesis of Compound (A11) Synthesis of9-(4-diphenylaminophenyl)-10-(3,4-diphenylphenyl)-anthracene (Compound(A11))

Under an atmosphere of argon,9-(4-chlorophenyl)-10-(3,4-diphenyl-phenyl)-anthracene (2.3 g, 4.4mmole), diphenylamine (0.9 g, 5.3 mmole, 1.2 eq),tris(dibenzylideneacetone)dipalladium(0) (0.1 g, 0.11 mmole, 5% Pd), atoluene solution of tri-t-butylphosphine (66% by weight, 0.05 ml, 0.16mmole, 0.7 eq to Pd) and sodium t-butoxide (0.6 g, 6.3 mmole, 1.4 eq)were suspended in anhydrous toluene (20 ml). The resultant mixture wasrefluxed for 8 hours. The reaction mixture was filtered and washed withtoluene, water and methanol, and a light yellow solid substance wasobtained. The obtained solid substance was suspended in boiling toluene(40 ml). After the suspension was cooled while being left standing, thesuspension was filtered, and a light yellow solid substance (2.2 g, theyield: 78%) was obtained. It was confirmed in accordance with ¹H-NMR andFDMS that the obtained product was Compound (A11).

Synthesis Example 7 Synthesis of Compound (A14) Synthesis of9-(4-diphenylaminophenyl)-10-(3,5-diphenylphenyl)-anthracene (Compound(A14))

Under an atmosphere of argon,9-(4-chlorophenyl)-10-(3,5-diphenyl-phenyl)anthracene (2.3 g, 4.4mmole), diphenylamine (0.9 g, 5.3 mmole, 1.2 eq),tris(dibenzylideneacetone)dipalladium(0) (0.1 g, 0.11 mmole, 5% Pd), atoluene solution of tri-t-butylphosphine (66% by weight, 0.05 ml, 0.16mmole, 0.7 eq to Pd) and sodium t-butoxide (0.6 g, 6.3 mmole, 1.4 eq)were suspended in anhydrous toluene (20 ml). The resultant mixture wasrefluxed for 8 hours. The reaction mixture was filtered and washed withtoluene, water and methanol, and a light yellow solid substance wasobtained. The obtained solid substance was suspended in boiling toluene(40 ml). After the suspension was cooled while being left standing, thesuspension was filtered, and a light yellow solid substance (2.5 g, theyield: 86%) was obtained. It was confirmed in accordance with ¹H-NMR andFDMS that the obtained product was Compound (A14).

Synthesis Example 8 Synthesis of Compound (A20) Synthesis of9-(9,9-didimethylfluoren-2-yl)-10-(4-(2,2-diphenyl-vinyl)phenyl)anthracene(Compound (A20))

Under an atmosphere of argon,9-(9,9-dimethylfluoren-2-yl)-10-bromoanthracene (2.8 g, 6.2 mmole),4-(2,2-diphenylvinyl)phenylboric acid (2.0 g, 6.7 mmole, 1.1 eq) andtetrakis(triphenylphosphine)palladium(0) (0.14 g, 0.12 mmole, 2% Pd)were suspended in toluene (20 ml). To the obtained suspension, a 2Maqueous solution of sodium carbonate (2.1 g, 20 mmole, 3 eq/10 ml) wasadded, and the resultant mixture was refluxed for 10 hours. The reactionmixture was filtered and washed with water and methanol, and a lightyellow solid substance was obtained. The obtained solid substance wassuspended in boiling toluene (30 ml). After the suspension was cooledwhile being left standing, the suspension was filtered, and a lightyellow solid substance (3.0 g, the yield: 78%) was obtained. It wasconfirmed in accordance with ¹H-NMR and FDMS that the obtained productwas Compound (A20).

Example 1

A glass substrate (manufactured by GEOMATEC Company) of 25 mm×75 mm×1.1mm (thickness) having an ITO transparent electrode was cleaned byapplication of ultrasonic wave in isopropyl alcohol for 5 minutes andthen by exposure to ozone generated by ultraviolet light for 30 minutes.The glass substrate having the transparent electrode lines which hadbeen cleaned was attached to a substrate holder of a vacuum vapordeposition apparatus. On the surface of the cleaned substrate at theside having the transparent electrode, a film ofN,N′-bis(N,N′-diphenyl-4-aminophenyl)-N,N-β-naphthyl-4,4′-diamino-1,1′-biphenyl(a film of TPD232) having a thickness of 60 nm was formed in a mannersuch that the formed film covered the transparent electrode. The formedfilm of TPD232 worked as the hole injecting layer. On the formed film ofTPD232, a film of N,N,N′,N′-tetrakis(4-biphenyl)-4,4′-benzidine (a filmof BPTPD) having a thickness of 20 nm was formed. The formed film ofBPTPD worked as the hole transporting layer. On the formed film ofBPTPD, a film of the above Compound (A1) having a thickness of 40 nm wasformed by vapor deposition. The formed film of Compound (A1) worked asthe light emitting layer. On the film formed above, a film of Alq shownin the following having a thickness of 10 nm was formed. The film of Alqworked as the electron injecting layer. Thereafter, Li (the source oflithium: manufactured by SAES GETTERS Company) as the reducing dopantand Alq were binary vapor deposited, and an Alq:Li film (the thickness:10 nm) was formed as the electron injecting layer (cathode). On theformed Alq:Li film, metallic aluminum was vapor deposited to form ametal cathode, and an organic EL device was prepared.

When a direct current voltage of 6 V was applied to the organic ELdevice prepared above, blue light was emitted at a luminance of 176cd/m² and an efficiency of the light emission of 2.2 cd/A.

The device was then subjected to the evaluation by the storage test at ahigh temperature. Namely, after the above device was sealed, the devicewas left standing in a thermostatic oven kept at 100° C. for 500 hours,and it was examined whether defects such as changes in the bright spotsand the color were found on the light emitting surface by observationusing a stereomicroscope of a magnification of 200 times. The resultsare shown in Table 1.

Examples 2 to 10

Organic EL devices were prepared in accordance with the same proceduresas those conducted in Example 1 except that compounds shown in Table 1were used in place of Compound (A1) used in Example 1. The voltageapplied to the devices, the luminance of emitted light, the efficiencyof light emission and the color of emitted light of the devices, theglass transition temperature Tg of the used compound and the results ofthe storage test of the devices at a high temperature are shown in Table1.

Comparative Example 1

An organic EL device was prepared in accordance with the same proceduresas those conducted in Example 1 except that Compound (C1) shown in thefollowing, which is an arylanthracene compound described in the U.S.Pat. No. 0,593,5721, was used in place of Compound (A1) used inExample 1. The voltage applied to the device, the luminance of emittedlight, the efficiency of light emission and the color of emitted lightof the devices, the glass transition temperature Tg of the used compoundand the results of the storage test of the device at a high temperatureare shown in Table 1.

Comparative Example 2

An organic EL device was prepared in accordance with the same proceduresas those conducted in Example 1 except that Compound (C2) shown in thefollowing, which is an arylanthracene compound described in JapanesePatent Application Laid-Open No. 2000-273056, was used in place ofCompound (A1) used in Example 1. The voltage applied to the device, theluminance of emitted light, the efficiency of light emission and thecolor of emitted light of the device, the glass transition temperatureTg of the used compound and the results of the storage test of thedevice at a high temperature are shown in Table 1.

Comparative Example 3

An organic EL device was prepared in accordance with the same proceduresas those conducted in Example 1 except that Compound (C3) shown in thefollowing, which is another arylanthracene compound described inJapanese Patent Application Laid-Open No. 2000-273056, was used in placeof Compound (A1) used in Example 1. The voltage applied to the device,the luminance of emitted light, the efficiency of light emission and thecolor of emitted light of the device, the glass transition temperatureTg of the used compound and the results of the storage test of thedevice at a high temperature are shown in Table 1.

TABLE 1 Compound Luminance Efficiency Storage of light of emitted oflight Color of Tg of test emitting Voltage light emission emittedcompound at high layer (V) (cd/m²) (cd/A) light (° C.) temperatureExample 1 (A1) 6.0 176 2.2 blue 108 good Example 2 (A2) 6.0 200 2.3 blue120 good Example 3 (A3) 6.0 161 3.1 blue 122 good Example 4 (A4) 6.0 1102.3 blue 115 good Example 5 (A5) 6.0 780 2.0 blue 114 good Example 6(A6) 6.0 180 2.8 bluish 112 good green Example 7 (A10) 6.0 250 2.9 blue128 good Example 8 (A20) 6.0 180 3.1 blue 124 good Example 9 (B1) 6.0260 2.2 blue 156 good Example 10 (B2) 6.0 313 3.1 blue 152 goodComparative (C1) 6.0 120 2.1 bluish ND crystallized Example 1 greenComparative (C2) 6.0 125 2.1 blue  95 crystallized Example 2 Comparative(C3) 6.0 153 2.5 blue 109 crystallized Example 3 * In the test ofstorage at a high temperature, the result was evaluated as “good” whenno defects such as changes in the bright spots and the color on thelight emitting surface were found, and as “crystallized” when defectssuch as changes in the bright spots and the color on the light emittingsurface were found. In the column of Tg, ND means that no Tg wasobserved in the measurement in accordance with the differential scanningcalorimetry (DSC).

As shown in Table 1, in Comparative Example 1 in which Compound (C1)having an excellent symmetry was used, defects appeared on the lightemitting surface due to crystallization, and the emitted light wasbluish green, i.e., the purity of the blue color was not excellent. InComparative Examples 2 and 3, crystallization took place even thoughCompounds (C2) and (C3) had asymmetric molecular structure in thehorizontal direction. This is considered to have taken place due to lowglass transition temperatures. Since the compounds of the presentinvention were asymmetric and had relatively high glass transitiontemperatures, the results of the storage test at a high temperature wereexcellent.

Example 11

A glass substrate (manufactured by GEOMATEC Company) of 25 mm×75 mm×1.1mm (thickness) having an ITO transparent electrode was cleaned byapplication of ultrasonic wave in isopropyl alcohol for 5 minutes andthen by exposure to ozone generated by ultraviolet light for 30 minutes.The glass substrate having the transparent electrode lines which hadbeen cleaned was attached to a substrate holder of a vacuum vapordeposition apparatus. On the surface of the cleaned substrate at theside having the transparent electrode, a film of TPD232 having athickness of 60 nm was formed in a manner such that the formed filmcovered the transparent electrode. The formed film of TPD232 worked asthe hole injecting layer. On the formed film of TPD232, a film of BPTPDhaving a thickness of 20 nm was formed. The formed film of BPTPD workedas the hole transporting layer. On the formed film of BPTPD, a film ofthe above Compound (A1) having a thickness of 40 nm was formed by vapordeposition. The formed film of Compound (A1) worked as the lightemitting layer. At the same time, a styrylamine-based light emittingmolecule (D1) shown in the following was added in an amount of 7% byweight. On the film formed above, a film of Alq having a thickness of 20nm was formed. The film of Alq worked as the electron injecting layer.Thereafter, Li (the source of lithium: manufactured by SAES GETTERSCompany) as the reducing dopant and Alq were binary vapor deposited, andan Alq:Li film (the thickness: 10 nm) was formed as the electroninjecting layer (cathode). On the formed Alq:Li film, metallic aluminumwas vapor deposited to form a metal cathode, and an organic EL devicewas prepared.

When a direct current voltage of 5.5 V was applied to the organic ELdevice prepared above, blue light was emitted at a luminance of 200cd/m² and an efficiency of the light emission of 5.5 cd/A. When thedevice was driven at an initial luminance of 500 cd/m² under a constantelectric current, the time before the luminance decreased to a half ofthe initial value (the half life) was 3,000 hours.

Comparative Example 4

An organic EL device was prepared in accordance with the same proceduresas those conducted in Example 1 except that Compound (C1) shown in theabove, which is an arylanthracene compound described in the U.S. Pat.No. 0,593,5721, was used in place of Compound (A1) used in Example 1.The voltage applied to the device, the luminance of emitted light, theefficiency of light emission and the color of emitted light of thedevice, the glass transition temperature Tg of the used compound and theresults of the storage test of the device at a high temperature areshown in Table 1.

When a direct current voltage of 5.5 V was applied to the organic ELdevice prepared above, blue light was emitted at a luminance of 180cd/m² and an efficiency of the light emission of 5.0 cd/A. When thedevice was driven at an initial luminance of 500 cd/m² under a constantelectric current, the time before the luminance decreased to a half ofthe initial value (the half life) was as Short as 1,500 hours.

INDUSTRIAL APPLICABILITY

As described in detail in the above, the organic EL device whichexhibits a great luminance of emitted light, a great efficiency of lightemission and a high purity of color, emits bluish light, is excellent instability at high temperatures and has a long life can be obtained byutilizing the novel aromatic compound of the present invention.Therefore, the organic EL device of the present invention is very usefulas the light source for various electronic instruments.

1. A novel aromatic compound represented by following general formula(A):A-Ar—B  (A) wherein Ar represents a substituted or unsubstitutedanthracendiyl group, B represents a substituted or unsubstituted arylgroup having 5 to 60 carbon atoms, or a heterocyclic group which has 2to 60 carbon atoms, wherein the aryl group or the heterocyclic group ismono-substituted with an alkenyl group or an arylamino group, Arepresents a group which is selected from groups represented by thefollowing general formulae (4) to (6):

wherein Ar₁ represents a substituted or unsubstituted aryl group having6 to 30 carbon atoms; the foregoing general formulae (4) to (6) may besubstituted with substituted or unsubstituted alkyl groups having 1 to30 carbon atoms or substituted or unsubstituted phenyl group; and A doesnot represent phenyl group substituted with an arylamino group when thegroup represented by B is substituted with an arylamino group.
 2. Anovel aromatic compound according to claim 1, wherein B in generalformula (A) represents a heterocyclic group which has 2 to 60 carbonatoms and is mono-substituted with an alkenyl group or an arylaminogroup or an aryl group which has 5 to 60 carbon atoms and ismono-substituted with an alkenyl group or an arylamino group.
 3. A novelaromatic compound represented by following general formula (B):A′-Ar—Ar—B  (B) wherein Ar represents a substituted or unsubstitutedanthracendiyl group, B represents a substituted or unsubstituted arylgroup having 5 to 60 carbon atoms, or a heterocyclic group which has 2to 60 carbon atoms, wherein the aryl group or the heterocyclic group ismono-substituted with an alkenyl group or an arylamino group, A′represents a group which is selected from groups represented by thefollowing general formulae (4) to (6):

wherein Ar₁ represents a substituted or unsubstituted aryl group having6 to 30 carbon atoms; the foregoing general formulae (4) to (6) may besubstituted with substituted or unsubstituted alkyl groups having 1 to30 carbon atoms or substituted or unsubstituted phenyl group; and A doesnot represent phenyl group substituted with an arylamino group when thegroup represented by B is substituted with an arylamino group.
 4. Anovel aromatic compound according to claim 3, wherein B in generalformula (A) represents a heterocyclic group which has 2 to 60 carbonatoms and is mono-substituted with an alkenyl group or an arylaminogroup or an aryl group which has 5 to 60 carbon atoms and ismono-substituted with an alkenyl group or an arylamino group.
 5. A novelaromatic compound according to claim 1, which is a material for organicelectroluminescence devices.
 6. An organic electroluminescence devicewhich comprises a cathode, an anode and an organic thin film layercomprising at least one layer containing a light emitting layer andsandwiched between the cathode and the anode, wherein at least one layerin the organic thin film layer comprises a novel aromatic compounddescribed in claim 1 singly or as a component of a mixture.
 7. Anorganic electroluminescence device which comprises a cathode, an anodeand an organic thin film layer comprising at least one layer containinga light emitting layer and sandwiched between the cathode and the anode,wherein the organic thin film layer comprises at least one of anelectron transporting layer and a hole transporting layer, and at leastone of the electron transporting layer and the hole transporting layercomprises a novel aromatic compound described in claim 1 singly or as acomponent of a mixture.
 8. An organic electroluminescence deviceaccording to claim 6, wherein the light emitting layer further comprisesan arylamine compound.
 9. An organic electroluminescence deviceaccording to claim 6, wherein the light emitting layer further comprisesa styrylamine compound.
 10. An organic electroluminescence deviceaccording to claim 6, wherein an electron transporting region or aninterface region between the cathode and the organic thin film layercomprises a reducing dopant.
 11. An organic electroluminescence deviceaccording to claim 6, which emits bluish light.